Penetrating a difficult hole

[Bokkierob]

When you’r fucking a dude for the first time and he’s struggling to take your cock and you’re only half-way in, what do you do? Pull out, keep pushing or grip his shoulders and force it deep up his hole. 

[Bimarried001]

From a bottom’s perspective, the thing to do is to ease it in. Tops don’t realize that once they get that cock in we will adjust. But forcing it in may feel good to the top but it will take the bottom some time to adjust to the pain. 
 

I’ve had guys force it in me so I know. 

[NordicBtm]

I would say pull out and give the bottom 30 seconds. Then go back in and go all the way in and adjust. In my experience it’s a quicker adjustment than forcing in on first go and less painful for the bottom.

[topblkmale]

29 minutes ago, Bokkierob said:

When you’r fucking a dude for the first time and he’s struggling to take your cock and you’re only half-way in, what do you do? Pull out, keep pushing or grip his shoulders and force it deep up his hole. 

 

find a better (loose) bottom

 

[pupHawaii]

how about adding more lube?

[ellentonboy]

I've been told I am tight but everyone, no matter their size, manages to get in - especially if I lay on my back.  The situation sometimes changes as guys say I feel tight inside, they find it either a turn on and many times it makes them cum, while others complain "come on - open up".  Well, your dick is already all the way in, so what is the problem.

In almost all situations I relax, they are "free to move about the cabin" and they can get off.  I've never said to stop or take it out, or it hurts,  A talented top knows that if they give the guy 15 seconds he'll relax, lay back and enjoy the ride.

 

[FelchingPisser]

49 minutes ago, Bokkierob said:

When you’r fucking a dude for the first time and he’s struggling to take your cock and you’re only half-way in, what do you do? Pull out, keep pushing or grip his shoulders and force it deep up his hole. 

Pull out and rim him until he is begging for it.

[phukhole]

Not having a huge dick, this isn't OFTEN a problem for me, BUT.... I would pull out and eat his hole. Let him loosen up and get wet with my tongue. I might slide a finger in now and again to help open him up, then when he's grinding his ass on my tongue, I'd resume the fucking.   It's all about making the bottom relax.   Now, if it was the star quarterback who had bullied me in public. I'd just grab his throat, call him a little bitch in his ear and shove it in while he whimpered.... not that I've done that before!

[norefusal]

i'm a tight bottom so i've tried all of the advice given above. here's my rating in order of best to worst: 

1. rimming etc. asses are like cunts. the more foreplay to get us in the mood the more we just open right up. it's almost shocking how wet down there the right guy can make me. 

2. pull out, pause, add more lube, try again, don't force. this is my go to when guys rush to the main event. 

3. walk away and find a "better" hole. this only happened to me once and i hope the guy is currently having his balls mauled by a wild dog in the most painful and prolonged way. what a dick move! 

[Marlin]

I pull back and eat his hole some more, hand him poppers and slowly try again....always works

[Hunter22]

For me it is usually depends on the angle and the position, and a slight change of the angle can work wonders to take it deep past my second hole 

[NWUSHorny]

Pull out, and leave him alone for a minute then either eat his hole or rub my dickhead on his hole until he starts opening up, usually works. If they want it bad enough we can usually find a way to get them relaxes and open.

[barefucker44]

10 hours ago, topblkmale said:

 

find a better (loose) bottom

 

Just keep gettin deeper and deeper.  Any hole can take any cock with enuf patience.

[Cubbtm4poz]

As a bottom who is a tight ass (lol the pun) I prefer to have the top take his time an pull out an then try pushing in again...But do not force it in as that will cause the bottom to tense up and tighten up....I would suggest using more lube and maybe finger the hole a bit to get it to loosen up...

[barefucker44]

8 minutes ago, Cubbtm4poz said:

As a bottom who is a tight ass (lol the pun) I prefer to have the top take his time an pull out an then try pushing in again...But do not force it in as that will cause the bottom to tense up and tighten up....I would suggest using more lube and maybe finger the hole a bit to get it to loosen up...

Agree.  Take time to open up your hole until the top can fuck freely and breed when he is ready